Amidoboronates: bringing together the synthesis of BN-heterocycles via a reductive coupling and dynamic covalent chemistry

This Perspective describes how amidoboronates open up new chemical space spanning the areas of BN-heterocycles and dynamic covalent chemistry. BN-containing heterocycles offer the potential to access new properties and reactivity compared to their C-C analogues. Amidoboronates are introduced as a new class of B-N heterocycles that can be synthesised in three isomeric forms (meso(5), rac(5) and rac(6)) from the reductive coupling of N-aryl iminoboronates. Furthermore, initial investigations on the dynamic covalent chemistry of amidoboronates are discussed, such as the reversibility of C-C bond formation following the reductive coupling and tuning the rac(5)/rac(6) ratio via dynamic covalent B-N and B-O bonds.

Automated summary

This Perspective describes how amidoboronates open up new chemical space spanning the areas of BN-heterocycles and dynamic covalent chemistry. BN-containing heterocycles offer the potential to access new properties and reactivity compared to their C-C analogues. Amidoboronates are introduced as a new class of B-N heterocycles that can be synthesised in three isomeric forms (meso(5), rac(5) and rac(6)) from the reductive coupling of N-aryl iminoboronates. Furthermore, initial investigations on the dynamic covalent chemistry of amidoboronates are discussed, such as the reversibility of C-C bond formation following the reductive coupling and tuning the rac(5)/rac(6) ratio via dynamic covalent B-N and B-O bonds.